chemistry letters · 8 eﬀective synthesis of 5-substituted buteno-lide derivatives by using...

Chemistry Lettershttp://www.csj.jp/journals/chem-lett/

Vol.36 No.1 CMLTAGJanuary, 2007 ISSN 0366-7022

Copyright � 2007 The Chemical Society of Japan

2 Alkyl Phosphinites: Versatile Synthetic In-termediates for Dehydration CondensationReactions

ROPPh2R2 R3

R1 SS

N

R1 R2

H N

O

OR2 R3

R1 N3

R1 R2

H C(CO2Et)3

R1 R2

H C(SO2Ph)CN

R1 R2

H CMe(CN)2

R2 R3

R1 N C

R1 OR2

Teruaki Mukaiyama and Hokuto Yamabe

Recent advances in the oxidation–reduction condensation reaction of alkyl phosphinites are described. The carbon–sulfur, carbon–carbon, or carbon–nitrogen bond forming reactions and cyanation, isocyanation reactions are established.These reactions proceed through inversion of configuration even when tertiary alkyl phosphinites are employed, providingthus, a novel route to chiral hydrosulfides, amines, nitriles, and isocyanides from easily available chiral alcohols.

Highlight Review

Letter

8 Effective Synthesis of 5-Substituted Buteno-lide Derivatives by Using Cinchonidine-de-rived Quaternary Ammonium PhenoxideCatalyst

R H

O+

O

OSiMe3 1) (10 mol %)CH2Cl2, –78 °C, 1 h

2) 1 M HClaq, THF

R

OH

OH

O

up to 97% ee (syn-isomer)

N

N

OH

H

CF3

F3C

OPh .HOPh

Hitoshi Nagao, Yoshinobu Yamane, andTeruaki Mukaiyama

C-2 Chemistry Letters Vol.36, No.1 (2007)

Copyright � 2007 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

10 The First Total Synthesis of Vinaxanthone,a Fungus Metabolite Possessing MultipleBioactivities

MeO CHO

HO

Vanillin (2)

O

O

HO

HO

HO2CO

O

OH

OH

CO2H

MeO

O

Me

Vinaxanthone (1)

MeO

MeO

MeO2C

O

OOMe

OMe

CO2Me

O

O

Me

11

11

O

Me

O

Kuniaki Tatsuta, Soko Kasai, Yuki Amano,Takahiro Yamaguchi, Masashi Seki, and SeijiroHosokawa

Electronic Supporting Information

12 Aza-Prins Reaction Promoted by TitaniumTetraiodide and Iodine

In the presence of titanium tetraiodide and iodine, olefins and acetylenes underwent aza-Prinsreaction to give 1,3-iodoamines in good yields.

EtO2C

N

Ar

TiI4−I2

Ts EtO2C Ar

NH ITs

Ar EtO2C Ar

NH ITs

Makoto Shimizu, Toru Baba, Shingo Toudou,and Iwao Hachiya

14 A Convenient, Catalyst-free Cross-couplingReaction of �-Sulfur-substituted Alkylstan-nanes with Acid Chlorides Leading to �-Sul-fur-substituted Ketones

O

R3 Cl+

SR1

R2 SnnBu3

O

R3

SR1

R2

mesitylene, reflux

A thermal cross-coupling reaction of -sulfur-substituted alkylstannanes with acid chlorides

proceeds to give the corresponding -sulfur-substituted ketones in good yields.

αα

Hirotaka Kagoshima and Naoshi Takahashi

16 Colorimetric Assay for Evaluating GlycosylFluoride-hydrolyzing Activity of Glycosidaseby Using Alizarin Complexon Reagent

F

OH2

Hydrolysis

OOH

HOOH

O

OH

OHO

OH

OH

F

La3+

O

OCH2

OHOH

NCH2COOH

CH2COOH

La3+-ALC complex

O

OCH2

OHOH

NCH2COOH

CH2COOH

La3+-ALC-F -

complex

F La3+

OOH

OHOH

O

OH

OOH

OH

OH

OH

Shin-ichiro Shoda, Keiko Shintate, MasakiIshihara, Masato Noguchi, and AtsushiKobayashi

18 Synthesis of an Enantiopure syn-Benzocyclo-trimer through Regio-selective Cyclotrimeri-zation of a Halonorbornene Derivative underPalladium Nanocluster Conditions OSiMe2t-Bu

t-Bu

tt -BuMe2SiO

OSiMe2

-BuMe2SiO

I

+NBu4-OAc

"Palladium Nanoclusters"

+NBu4

-OAc

-OAc+NBu4

+NBu4

+NBu4

-OAc-OAc

Shuhei Higashibayashi and Hidehiro Sakurai


Chemistry Letters Vol.36, No.1 (2007) C-3


20 Synthesis of Oxy Aminated [60] and [70]Full-erenes with Cumene Hydroperoxide asOxidant

O

NR2

NR2

R2N NR2

NR2R2N O

HNR2+

ROOH

[60]fullerene [70]fullerene

Loıc Lemiegre, Takatsugu Tanaka, TakeshiNanao, Hiroyuki Isobe, and Eiichi Nakamura


22 A Facile Synthesis of N-[2-(Trifluoro-methyl)allyl]amides and Their Transforma-tion into Angularly TrifluoromethylatedBicyclic Cyclopentenones

TsN

CF3

O

R1

R3

NHTsR2

CF3sec-BuLiCF3

Br

CF3

Li

R1

CF3TsN

R1

R3

Co2(CO)8

R1R2C=NTs

Ryo Nadano and Junji Ichikawa

24 Low-valent Niobium-mediated Synthesis ofIndenes: Intramolecular Coupling Reactionof CF3 Group with Alkene C–H Bond

CF3

R3

R2

R1NbCl5 30 mol%

LiAlH4 5 mol. amt.

Dioxane, reflux, 3 hR1

R2

R3

57−68%Kohei Fuchibe, Ken Mitomi, and TakahikoAkiyama


26 Chloroform Is Not Solvent but Activator forCobalt Complex Catalyst of EnantioselectiveBorohydride Reduction

O OH

NaBH4, EtOH,HOO

in CHCl3 : 91% eein THF : 40% eecat.CHCl3 in THF:

91% ee

O

N N

OO OCo

1 mol%

N O

N OCo

C

O

H

H

Na+

H

Cl

Cl

H

Ai Kokura, Saiko Tanaka, Haruna Teraoka,Atsushi Shibahara, Taketo Ikeno, TakushiNagata, and Tohru Yamada

28 A New Synthetic Method for Methyl Ketonesfrom Carboxylic Acids Using Metallic Stron-tium and Methyl Iodide

R OH

O

R

OH

R

O2.0 equiv.Sr

THF (10 mL)

+

Total yield 76–50%(A:B = 93:7–86:14)

0.9 equiv.NaH

1.0 equiv. × 2MeI

A B

Carboxylic acids reacted with metallic strontium and methyl iodides to give methyl ketonespreferentially in moderate to good yields.

Norikazu Miyoshi, Tsuyoshi Matsuo, MasashiAsaoka, Aki Matsui, and Makoto Wada



30 Asymmetric Autocatalysis Induced by Octa-hedral Tris(acetylacetonato)chromium(III)Complex as a Homogeneous Chiral Initiator Cr

O

O

O

O

O

O

N

N

+t-Bu t-Bu

CHO

Cr

O

O

O

O

O

O

∆-(–)-Cr(acac)3Λ-(+)-Cr(acac)3 N

N

OHN

N

t-Bu

OH

AsymmetricAutocatalysis

AsymmetricAutocatalysis

SR

Zn2

Enantioenriched(R )-Alkanol

Enantioenriched(S )-AlkanolTsuneomi Kawasaki, Toshiki Omine, Mirai

Sato, Yosuke Morishita, and Kenso Soai

32 Transformations of N-Allyl-N-(phenylethyn-yl)arenesulfonamides into 2,2-Disubstituted4-Pentenenitriles through Aza-Claisen Rear-rangement that Follows Carbomagnesiation C C NSO2ArPh

R –MgBrcat. CuBr•Me2S

Ether, rtthen DME/Ether, ∆

C NC

RPh

R2

R1

R3 R1R2 R3

Hiroto Yasui, Hideki Yorimitsu, and KoichiroOshima

34 Chiral Scandium-catalyzed Highly Stereose-lective Ring-opening of meso-Epoxides withThiols

O R2SH

Ligand 1 (12 mol%)Sc(OTf)3 (10 mol%)

DCM, rt, 4−24 h

R1

R1

+R1

SR2R1

OH

NN

OH HO

tButBu

41−87% yield50−97% ee

Chikako Ogawa, Naiwei Wang, and ShuKobayashi

36 Studies toward Stable Analogues of Guano-fosfocins. Synthesis of the Protected Deriva-tive of 8-(5a-Carba-�-D-mannopyranosyl-oxy)purine Nucleoside

As a preliminary study directed towards the synthesis of a stable analogue of theguanofosfocins, a methylene analogue of the endocyclic oxygen atom in the mannosemoiety, was designed.

N

NN

HN

NHTr

O

OO

TBDPSOO

OBnOTBSO

OBnOS

OO

NaH

DMF, r.t., 15 min DMF, 50 °C, 23 h

H2SO4–THF–H2O(3:300:1)

r.t., 1.3 h

N

NN

N

NHTr

O

OO

TBDPSOO

BnOTBSO

OHBnO

69%

Hideyuki Sugimura and Naoya Hosogai

38 Iron(III) Chloride-catalyzed ReductiveEtherification of Carbonyl Compounds withAlcohols

R1 R2

O

R1 R2

OR

+Et3SiH

cat. FeCl3ROH

up to 97%

(R1 = aryl, alkyl; R2 = H, alkyl; R = 1°, 2°, 3°)Katsuyuki Iwanami, Kentaro Yano, andTakeshi Oriyama



40 An Expeditious Synthesis of Lasofoxifeneand Nafoxidine via the Novel Three-compo-nent Coupling Reaction H

O

OMe

OMeSiMe3

rt, 2 h++

HfCl4

78%

Nafoxidine

PivO

PivO

OPiv

IMeO

I(py)2BF4

41%

-78 oC, 2 h

CH2Cl2 DMSO

89%

90 oC

OH

MeO

Lasofoxifene

t-BuOKBF3 • OEt2

Yoshiyuki Sano, Kenya Nakata, TakafumiOtoyama, Sei Umeda, and Isamu Shiina

42 Claisen Rearrangement Strategy in AlkenylDihydropyran Leading to Total Synthesis of(+)-�-Vetispirene and (�)-Agarospirol

Total synthesis of (+)- -vetispirene and (−)-agarospirol based on a Claisen rearrangementhas been achieved. This is the first example of a Claisen rearrangement in an enantio-enriched alkenyl bicyclic dihydropyran system with perfect asymmetric transmission.

O

OP

OOP

99% ee 99% ee

ClaisenRearrangement

(+)-α -Vetispirene

HO

(−)-Agarospirol

73% yield

α

Atsuo Nakazaki and Susumu Kobayashi


44 Catalytic Asymmetric Addition of Alkynyl-zinc Reagents to Nitrones

Atsuko Konishi, Weilin Wei, MasatoKobayashi, Shuhei Fujinami, Yutaka Ukaji,and Katsuhiko Inomata


46 Enantioselective Epoxidation of ConjugatedZ-Olefins with Newly Modified Mn(salen)Complex

R2R1 3, aq. NaOCl R2R1 OR1 = unsaturated group

PPNO

N N

O OMn

R

R R

RCl

3: R = t-Hex

88-96% ee

Hiromichi Egami, Ryo Irie, Ken Sakai, andTsutomu Katsuki

48 Reductive Ti-crossed Claisen Condensationbetween Methyl �-Bromocarboxylates andAcid Chlorides Utilizing a TiCl4–PPh3–N-Methylimidazole Reagent

R1N

O

NMe

Cl-

ClR1

ON NMe

R2

OMe

OTiCl3

R3

R1

O O

OMe

R2 R3

++

TiCl4 - PPh3

Highly Reactive Acyl ammonium Intermediate

Ti - enolate

α-mono or α,α-disubstitutedβ-ketoesters

33 examples; 73 - 96%R2

OMe

O

BrR3

Akira Iida, Syogo Nakazawa, HidefumiNakatsuji, Tomonori Misaki, and Yoo Tanabe



50 Alkylation of N-Protecting Group-freeIndole with Vinyl Ketones Using Iron SaltCatalyst

NH

NH

O

R2

(R1 = H)R2

O

NH

O

R2

+

R2

O

R1R1

R1

R1

Fe(BF4)2 • 6H2O(3 mol %)

CH3CN, IL, or MeOHat rt under air

Toshiyuki Itoh, Hiroyuki Uehara, Koji Ogiso,Shun Nomura, Shuichi Hayase, and MotoiKawatsura


52 Rh(II)-catalyzed Isomerization of 2-Aryl-2H-azirines to 2,3-Disubstituted Indoles

2H-Azirines

cat. Rh2(OCOCF3)4

Indoles

R1

R2

NNH

R2

R1

ClCH2CH2Clrt − reflux

R1 = aryl, allyl, CN, N

O

O

R2 = Me, ,

34−91%Shunsuke Chiba, Gaku Hattori, and KoichiNarasaka


54 ‘‘contra-Michael’’ Addition of Alkyllithiumsto Silicon- and Phenyl-substituted �,�-Unsaturated Amides in the Presence of t-BuOK

Tomoko Hinago, Nana Teshima, SatokoKenmoku, Tiyako Kamata, Nahoko Terauchi,Nao Chiba, Chikako Satoh, Aya Nakamura,and Morio Asaoka

56 Iron-catalyzed Direct-type Hydroxymethyla-tion of 1,3-Dicarbonyl Compounds in Water

+ aq. HCHO Fe(NO3)3•9H2O (5 mol %)SDBS (15 mol %)

H2O, rtR1

O

R2

O

R1

O

R2

O

OH

Chikako Ogawa and Shu Kobayashi

58 Helix-dimer–Random-coil Thermal Switch-ing Process of Ethynylhelicene HeptamerHighly Sensitive to Its Environment

2

heatingcooling

thermal input

various ∆ outputsεsolvent perturbation

Hiroki Sugiura and Masahiko Yamaguchi




60 1,3-Dipolar Cycloaddition of Ethyl Diazoace-tate to Alkynes in the Pores of Zeolite NaY

up to 97% YieldZeolite NaY

R2R1

N N CHO

OEt NHN

R2

CO2EtR1

Zeolite NaY promotes 1,3-dipolar cycloaddition of ethyl diazoacetate to alkynes having anelectron-withdrawing group to afford the corresponding functionalized pyrazoles in highyields.

Keijiro Kobayashi, Yuta Igura, Shouhei Imachi,Yoichi Masui, and Makoto Onaka


62 Synthesis of Unsymmetrically and HighlySubstituted Thiophenes Utilizing Regioselec-tive Ring-expansion of gem-Dichlorocyclo-propyl Ketones with Lawesson’s Reagent

SCl

R1 Me

R2

SR1 R2

MeCl

O

R2

Me

ClCl

R1Lawesson's reagent

(R1 = H, Me)

(R1 = Ph)

PhB(OH)2

cat. PEPPSI-IPr (2 mol %)

K2CO3

SPh

R1 Me

R2

SR1

Ph Me

R2

1

2

3

4

5

Ring-expansion of aryl gem-dichlorocyclopropyl ketones 1 using Lawesson’s reagent afforded

diphenylthiophenes 5, respectively.

unsymmetrically and highly substituted 5-chloro and 3-chlorothiophenes 2 and 3 withexcellent regioselectivity. The Suzuki−Miyaura coupling of 2 and 3 with PhB(OH)2 wassuccessfully performed to give 2-aryl-3-methyl-5-phenylthiophenes 4 and 2-aryl-3-methyl-4,5-

Takao Nagano, Hiroki Kimoto, HidefumiNakatsuji, Jiro Motoyoshiya, Hiromu Aoyama,Yoo Tanabe, and Yoshinori Nishii

64 Highly Diastereoselective Conjugate Addi-tion of Aryllithium to Chiral �-NitrostyreneDerivative: An Application to the Asymmet-ric Synthesis of 4-Aryl-1,2,3,4-tetrahydroiso-quinoline

NO2

O

O

Et

Et

ArLi (1.5 equiv.)

NO2

O

O

Et

Et

Ar

NH

Ar

up to 98% de

THF, –100 °C, 30 min

Masatoshi Asami, Ayako Taketoshi, KeitaMiyoshi, Hayato Hoshino, and KazuhisaSakakibara


66 W(CO)5(L)-catalyzed Cyclization of !-Ace-tylenic Silyl Enol Ethers for the Preparationof Nitrogen-containing Cyclic Compounds OTIPS

NR

R'

n

W(CO)6 / hν

NR

OR'

Hn N

R

OR'

Hn

and/or

major in THF major in toluene

Antoine Grandmarre, Hiroyuki Kusama, andNobuharu Iwasawa

68 Ultracentrifuge-mediated Diels–Alder Reac-tion in a Two-phase System of Water andChloroform

Ambient condition : Yield 29 %

ultracentrifuge 100,000 rpm

Two phase

water oil

O

O−t -Bu+

25 °C, 50 minCO2−t -Bu

CO2−t -Bu+

High pressure condition under ultracentrifuge : Yield 82 %

1 atm

centrifugal forceHigh pressure

water organic phase

Ultracentrifugation has been successfully applied to the Diels−Alder reaction of acrylate esteror methacrolein with cyclopentadiene under water−CHCl3 two-phase conditions, affording theDiels−Alder adducts in good yield. The Diels−Alder reaction proceeds in the lower organicphase under ultracentrifugation-induced high pressure with the upper water phase acting like aweight.

Yujiro Hayashi, Mitsuhiro Takeda, MitsuruShoji, and Masataka Morita



70 Polyoxometalate-assisted One-step Fabrica-tion of Porous Nanorods of �-FeOOH andthe Facile Transition to Hematite

Uniform porous β-FeOOH nanorods of 10−20 nm are controllably fabricated by directhydrothermal treatment of FeCl3 and dilute tungstophosphoric acid H3PW12O40 (PW12)solution. Porous structure of the nanorods is studied with N2 adsorption−desorption. Hematite(α-Fe2O3) nanorods with similar morphologies were obtained by annealing these β-FeOOHnanorods.

β

βα

Baodong Mao, Zhenhui Kang, Enbo Wang,Chungui Tian, Zhiming Zhang, Chunlei Wang,and Siheng Li


72 Synthesis and Structure of Optically Active1,12-Diethyl- and 1,12-Diisopropylbenzo[c]-phenanthrenes: An Isopropyl Group CanBe Smaller than a Methyl Group

AD

RR

Dihedral angle of the A/D ring 41.8°

R = Me

47.9° 45.2°

Strain of helicene R = Et R = i -Pr

Hiroki Sugiura, Daisuke Sakai, Harunori Otani,Kazuhiro Teranishi, Yusuke Takahira, RyoAmemiya, and Masahiko Yamaguchi


74 (ET)3(Br3)5: A Metallic Conductor withan Unusually High Oxidation State of ET(ET = Bis(ethylenedithio)tetrathiafulvalene)

Electrochemical oxidation of ET with Br− yields a

bromine chemical species is all Br3− and the formal

metallic crystalline product, (ET)3(Br3)5, in which the

charge of ET becomes an unusually high value (5/3+).Hiromi Minemawari, Toshio Naito, andTamotsu Inabe


76 Peptide Ligation Using a Building BlockHaving a Cysteinyl Prolyl Ester (CPE) Au-toactivating Unit at the Carboxy Terminus

A peptide building block, not having a thioester moiety but a cysteinyl prolyl ester (CPE)autoactivating unit at the C-terminus is used in thiol-mediated ligation, such as native chemicalligation.

SH

O

N

O

O

HN

O R1

H2N

HS

O

NH

HS

O

O

+peptide 1 peptide 2

peptide 2peptide 1

Toru Kawakami and Saburo Aimoto

78 Highly Ordered Structures Self-assembledby NaDC under Metal-ion-mediation

The fan-like structural aggregates of sodium deoxycholate precipitates changed totree-like fractal structrues with the concentration of metal ions increasing.

4 × 10−3 mol/L NaDC 4 × 10−3 mol/L NaDC

1 × 10−1 mol/L NaCl

Ying-Te Wang, Xiao-Qing Yan, Hui-Li Ma,and Wei-Jun Jin



80 Morphology-controlled TiO2 NanoparticleSynthesis via Aerosol-assisted Vapor-phaseReactions

200 nmb) 200 nmc)

500 nma)

TiO2 particles with various morphologies have

nanoparticles varying from single crystal

grown on a core particle.

been synthesized via aerosol-assisted vapor-phasereactions. The results showed the controlledformation of variously shaped crystalline TiO2

nanoparticles to unique dendritic nanostructures

Isao Matsui and Hiroyuki Fujimori

82 Regio- and Stereoselective Ring Opening ofEpoxides and Aziridines Using ZirconylChloride: An Efficient Approach for the Syn-thesis of �-Chlorohydrins and �-Chloro-amines

R

O ZrOCl2MeCN

ROH

Cl

+R

Cl

OH

R

NTs ZrOCl2MeCN

RNHTs

Cl

RCl

NHTs

+

80 – 98%

85 – 92%

20 – 70 min r. t.

0.5 – 8 h r. t.Biswanath Das, Maddeboina Krishnaiah, andKatta Venkateswarlu

84 Quercetin-induced Conformational Changeof Human Serum Transferrin

Conformaitonal change of Tf induced by quercetin is obtained via non-covalent bonds, whichprovides a potential method to use Tf for target-oriented delivery of drug molecules.

Hongyan Du, Junfeng Xiang, Yalin Tang, andZhanli Wang


86 Photoluminescence of Eu(DBM)3Phen-em-bedded Silica Nanospheres Synthesized inMicroemulsion

Eu(DBM)3Phen-embedded silica nanospheres with 40-nm diameter were synthesized through aW/O microemulsion method. Low-temperature decay curves of the Eu(DBM)3Phen-embeddedsilica nanoparticles and laser selective excitation spectra confirm that the different luminescentcenters exist in nanospheres.

577 578 579 580 581 5820.0

0.2

0.4

0.6

0.8

1.0

8

B

A

7

6

5

4

3

2

1

Inte

nsity

(N

orm

aliz

ed)

Wavelength /nm

Yan Wang, Weiping Qin, Jisen Zhang,Chunyan Cao, Jishuang Zhang, Shaozhe Lu,Ye Jin, Guodong Wei, Guofeng Wang, and LiliWang

88 CdS Quantum Dots Sensitized TiO2 Sand-wich Type Photoelectrochemical Solar Cells

CdS quantum dots sensitized TiO2 film(sensitized film area: 5 × 5 mm2)

F–SnO2 glass

Pt counter electrode

QDs sensitized TiO2 film

Spacer

TiO2 particleQD

CdS–TiO2 Sandwich Type Photoelectrochemical Solar Cells

Yasuhiro Tachibana, Hitomi Y. Akiyama,Yasuhide Ohtsuka, Tsukasa Torimoto, andSusumu Kuwabata




90 Crystal Structure and Magnetic Property ofTwo Novel 1-D Cobalt(II) Assemblies

Naoji Masuhara, Shinya Hayami, NatsukoMotokawa, Aya Shuto, Katsuya Inoue, andYonezo Maeda


92 Ability of Fluorinated AOT Analogues forMicroemulsion Formation in Carbon Diox-ide To clarify the relationship between the structure and the ability

of fluorinated AOT analogues for W/scCO2 microemulsion

formation, we examined the AOT analogues having fluoroalkyl

groups of different lengths, and CF2H, CF3, or CF(CF3)2

moieties at the terminal of the fluorinated CO2-philic tails. It

was found that both the length and the structure of fluoroalkyl

groups contained in AOT molecules affect the ability.

Rf = — CH2CHFCF3

— CH2(CF2)4H — CH2(CF2)3F — CH2CH2(CF2)4F — CH2(CF2)6H — CH2CH2(CF2)6F — CH2CH2(CF2)2CF(CF3)2

— CH2CH2(CF2)4CF(CF3)2

— CH2CH2(CF2)8F

O

O

O

ONa+SO-3

Rf

Rf

Takabumi Nagai, Kazuhisa Fujii, KatsutoOtake, and Masahiko Abe

94 Effect of Hydrogen on Polymerizing theFullerene Molecules in the Single-wall Car-bon Nanotubes

Yoko Fujita, Shunji Bandow, and Sumio Iijima

96 Preparation of a Carboxylate-binding Mono-nuclear Iron(II) (�)-Sparteine Complex withStructural Distortion and Its Reaction withOxidants

N N FeII

OO

O O

H2O2, t –BuOOH, PhIO or m CPBAC2H5CN

CH3CHO

CN–

[FeII((−)–sp)(OBz)2]

Self-oxidation of (–)-sp

and

Takeshi Okumura, Shinya Hayami, TomohiroOzawa, Yasuhiro Funahashi, Yonezo Maeda,and Hideki Masuda


98 Visual Color Sensor for Indole Vapors

The film color changes from yellow to

vapor in air followed by treatment with

detection of indole and pyrrolevapors by naked eyes without heavy

magenta upon exposure to indole

aq H2O2 solution, thus allowing visual

instrumentations.

Yoshiumi Kohno, Takeshi Okubo, and RyokaMatsushima



100 Layered Hybrid Thin Film of MolybdenumTrioxide with Poly(2,5-dimethylaniline) forGas Sensor Sensitive to VOC Gases in ppmLevel

Toshio Itoh, Ichiro Matsubara, Woosuck Shin,and Noriya Izu

102 Tributylphosphane-catalyzed Condensationof Alcohol and Carboxylic Acid with DCCDirected toward Rotaxane Synthesis

DCC, Bu3PNH2

O

O

O

O

O

O

O

O

OH

PF6

R COOHNH2

O

O

O

O

O

O

O

O

O

PF6

R

O

Base Sensitive Substrate

+

Neutral Acylation Catalyst

good to excellent yields

Yoshimasa Makita, Nobuhiro Kihara, andToshikazu Takata

104 Oxalic Acid-promoted Preparation of Di-thioacetals from Carbonyl Compounds orAcetals

R1 R2

O

R1 R2

RS SR+ RSH

CH3NO2

(COOH)2

R1 R2

OMeMeOor

Oxalic acid-catalyzed syntheses of dithioacetals fromcarbonyl compounds or acetals are described.

Hideyoshi Miyake, Yuichi Nakao, and MitsuruSasaki

106 Effects of Vacuum Ultraviolet Light Illumi-nation on the Residual Stress in Sol–Gel-de-rived Titanium Dioxide Films

TiO2 101

Naoki Arimitsu, Akira Nakajima, KeisukeSaito, Yoshikazu Kameshima, and KiyoshiOkada


108 A Novel Self-aggregates of PhthalocyanineBased on Zn–O Coordination

N

N N

N

N

N NN

Zn

O

O

O

O

R

R

R

R

N

N N

N

N

N NN

Zn

O

O

O

O

R

R

R

R

N

N N

N

N

N NN

Zn

O

O

O

O

R

R

R

R

CH3OH

300 400 500 600 700 8000.0

0.5

1.0

1.5

2.0

0.0 0.5 1.0 1.5 2.0 2.5 3.0 3.50.0

0.2

0.4

0.6

0.8

1.0

∆A a

t 74

1 n

m

Concentration of methanol /mol L-1

Ab

sorb

ance

Wavelength /nm

Xin Huang, Fuqun Zhao, Zhongyu Li, LeiHuang, Yingwu Tang, Fushi Zhang, andChen-Ho Tung




110 NegativeMagneto-resistance Observed on anIon-radical Salt of a TTF-based Spin-polar-ized Donor

Michio M. Matsushita, Hironori Kawakami,Yuzo Kawada, and Tadashi Sugawara


112 Fabrication andMagnetic Properties of Mul-tiferroic BiFeO3 Nanotube Arrays

Xueqin Xu, Tian Qian, Genqiang Zhang, TaoZhang, Guang Li, WeiWang, and Xiaoguang Li

114 Simple Vanadium(V) Catalyst for Oxidationof Alkane with O2 under Mild Conditions

1/2 O21 atm

OXOX

V5+

O

V5+

O – O

AcOH, 393 K 75% 25%

Simple Catalytic Oxidation System

44% Yield440 TON

in 10 h

Hirokazu Kobayashi and Ichiro Yamanaka

116 Direct Visible Spectral Analysis of SolidSamples by Optical Waveguide Spectroscopydue to Adsorbed Sample Molecules afterSublimation

300 400

0.00

0.05

0.10

0.15

0.20 t (min)

Abs

orba

nce

/arb

uni

t

Wavelength /nm

0 10 20 30 40 50 60 70 80

Visible spectra of solid samples wereobtained by optical waveguide (OWG)spectroscopy. The spectra were confirmedto be due not to the powder samplesthemselves but to molecules sublimedfrom the solid samples and adsorbed on thewaveguide.

Hiromi Takahashi, Kyoko Fujita, and HiroyukiOhno


118 Preparation of Highly Ordered MesoporousThiophene–Silica with Spherical Macro-structure

H+ (aq)

Template removal

CH3O CH2CH2O CCH2O CCOH CH2CH2O CH3

O CH3

x y z x

O

SSi(OEt)3Si(OEt)3

Eun-Bum Cho and Dukjoon Kim




120 Preparation of Polymeric Nanocapsulesby Gamma-ray-initiated MiniemulsionPolymerization

Shijie Wang, Yunchen, and Zhicheng Zhang


122 Selective Epoxidation of Cyclohexene by aSquare-planar Ru Complex Immobilizedinto Mesoporous Silicate FSM-16

O

N NN

ON

OPhPh

Ru

Si

O

PhIOt -BuOOH

Ru complex immobilized into FSM-16

Takeshi Okumura, Hideki Takagi, YasuhiroFunahashi, Tomohiro Ozawa, YoshiakiFukushima, Koichro Jitsukawa, and HidekiMasuda


124 BSSE-corrected Three-body InteractionEnergy in the Recognition of GC Base Pairby Asparagine

Binding of asparagine side chain to GC base pair is stronger in the major groove than in theminor groove complex. Both two- and three-body interaction energies contribute almostequally to the superiority in the binding energy of the major groove complex.

Major groove recognition Minor groove recognition

Tomoki Yoshida and Misako Aida


126 Ellipsoidal Carbon Capsules EncapsulatedMagnetite Nanorods

α-Fe2O3@Air@polypyrrole Fe3O4@Air@carbon

Uniform ellipsoidal Fe3O4@Air@carbon

nanorods have been fabricated by in situ3O4capsules encapsulated movable Fe

carbonization–reduction process using

ellipsoidal spheres as template.sandwich @Air@polypyrroleα-Fe2O3

Ling-Yun Hao, Shou-Hu Xuan, Xing-LongGong, Rui Gu, Wan-Quan Jiang, and Zu-YaoChen


128 Enhanced Photocatalytic Activities of Core–Shell Au–Titanate Nanoparticles

By using 4,5-dihydroxy-1,3-benzenedisulfonic

fabricated Au–titanate core–shell nanoparticles

molecules not only played a role as a reduction

alkoxide led to the formation of Au–titanate

sols and exchanging solvent were important

nanocomposites had high photocatalytic effects

acid disodium salt (Tiron), we’ve successfully

and estimated their photocatalytic activities.Tiron

nanoparticles. We demonstrated that such

for the decomposition of Methylene Blue.

agency to reduce Au ions but also as a surfactantin ionized form. Moreover, addition of titanium

nanocomposites. Controlled centrifugation of Au

factors for the formation of Au–titanate core–shell

Tomokatsu Hayakawa, Mamiko Hori, C.Pagnoux, J. F. Baumard, and Masayuki Nogami



130 Readily Regenerative and Air-stable Palla-dium(0) Catalyst with Tris[2-(diphenylphos-phino)ethyl]phosphine Tetrasulfide for C–CCoupling Reactions

P

P

PP

O

O

SS

SPd0(dba)

Regenerative and recyclable phosphine sulfide Pd0 catalyst

P

P

PP

S

S

SS

Pd0(dba)

Sen-ichi Aizawa, Mitsuyoshi Tamai, MaiSakuma, and Asari Kubo


132 Bioelectrocatalytic Reduction of O2 Cata-lyzed by CueO from Escherichia coliAdsorb-ed on a Highly Oriented Pyrolytic GraphiteElectrode

-0.6

-0.4

-0.2

0.0

i / m

A c

m−2

0.60.40.20.0

E / V vs. Ag/AgCl

with O2

without O2

Adsorbed CueO

Electrode

O2

2H2O

e-

e-

Yuko Miura, Seiya Tsujimura, Yuji Kamitaka,Shinji Kurose, Kunishige Kataoka, TakeshiSakurai, and Kenji Kano

134 Consequence of a Defect on the TerahertzSpectra of L-Asparagine Monohydrate

0.5 1 1.5 2 2.50

10

20

mol

ar a

bsor

ptio

n co

effic

ient

/ M

-1cm

-1

frequency / THz

AsnAsn + 4.6% AspAsn + 12.3% Asp We measured the terahertz vibrational

spectra of a solid solution of L-asparagine

spectrometer. THz spectroscopy is aneffective tool for detecting point defects

and L-aspartic acid monohydrate at 0.5to 6.0 THz using a GaP Raman THz

in a molecular crystal.

Jun-ichi Nishizawa, Takenori Tanno, TakashiYoshida, and Ken Suto

136 Selective Visual Determination of Vana-dium(V) Ion in Highly Acidic Solution UsingDesferrioxamine B Immobilization Cellulose

VV

pH<1

400 500 600 7000

0.2

0.4

0.6

0.8

1

Wavelength / nm

Ref

lect

ion

abso

rptio

n

Simple and selective determination method of VV ion was developed. The proposed methodwas succeeded by the immobilization of desferrioxamine B on cellulose paper. This indicatorpaper works in strong acidic condition, and this was quantitatively and rapidly colored.

Yoshitaka Takagai, Hitoshi Yamaguchi, ToshioKubota, and Shukuro Igarashi

138 Efficient Synthesis of Amylbenzenes overZeolite Catalysts

BetaAl

Amylbenzenes

Liquid-phase 3.5 MPa

+

Huanyan Zhang, Yueming Liu, Haihong Wu,Yongwen Jiang, Mingyuan He, and Peng Wu



140 Effect of Arginine at Type 2 Cu Site on Spec-troscopic Features and Enzymatic Activity ofCopper-containing Nitrite Reductase

Active site of Cu-containing nitrite reductase having Arg at the type 2 Cu site

Kazuya Yamaguchi, Aiko Tsuda, MasakiNojiri, and Shinnichiro Suzuki


142 Self-assembled Gold Nanoparticle Chains inPresence of Silver Ions

Assembling gold nanoparticles into one-, two-, and three-dimensional

sensor field, etc. Usually, for an assembly process, templating

viruses, and other predesigned nanostructures. For further study inthis area, assembling gold nanoparticles into 1D nanostructures by

this article, gold nanoparticles chains were fabricated by introducing

acid (MSA). For a new application, silver ions were introduced to

nanostructures has shown to be useful in electronic, optical, and

techniques are utilized, in which the templates include DNA, protein,

silver ions into the reactants including HAuCl4 and 2-mercaptosuccinic

template-free wet-chemical approaches would be highly desirable. In

nanochains by adjusting the content of silver ions.

adjust the lengths of gold nanochains by control the content of silverions. By changing the content of silver ions, the nanochains obtainedcould change from several tens nanometers to several micrometers.Compared with the methods provided by others, our strategy hasseveral advantages. First, the process of assembly is simple, and notemplate is needed. Second, the lengths of 1D assemblies is stronglybased on the content of silver ions. It is possible to prepare longer

Lanlan Sun, Yonghai Song, Gang Wei, LiWang, Cunlan Guo, Yujing Sun, and Zhuang Li

144 Exfoliation-free Nanosheet Synthesis ofTransition-metal Hydroxynitrate and ItsTransformation to Oxide Particulate Nano-sheet

Hongtao Cui, Marcos Zayat, and David Levy


146 A Simple Method to the Fabrication ofRectangular Co3O4 Nanosheets

Rectangular Co3O4 nanosheets with the thickness ofabout 50−100 nm were fabricated by calcining theisomorphological Co(CO3)0.35Cl0.20(OH)1.10 precursor,which were produced via the reaction of CoCl2 andCO(NH2)2 in the presence of PEG-10000.

Xiaomin Ni, Jimei Song, Dongguo Li,Yongfeng Zhang, and Huagui Zheng

148 In Situ Measurement of Individual W/OMicroemulsions of Aerosol OT in Dodec-ane/Water Extraction System by TotalInternal Reflection Laser Light ScatteringMicroscopy

In situ total internal reflection laser light scattering microscopy with a thin-layer two-phase microcell (right figure) allowed one to observe dynamic behaviors of W/O microemulsions of aerosol OT in a dodecane/water extraction system. Manymicroemulsions appeared as scattering particles in the laser

beam with dark background(indicated by arrows in left figure). The microemulsions were formed at the interface and diffusedaway into the dodecane phase, whereas some of them suddenly vanished atthe interface. Hydrodynamic radius of the individual microemulsions,which was obtained from the analysis of their Brownian motion in thedodecane phase, was in a range of 50–250 nm.

5 µm Satoshi Tsukahara, Haruyasu Kitaguchi, andHitoshi Watarai



150 Zinc(II) and Copper(I)–Ferrocenedicarbox-ylate Polyhedron and Polygon

Space-filling model depicting efficient packing offour different square-planar ferrocenedicarboxylate-tetranuclear cupurous clusters (violet = copper; red= oxygen,; green, blue yellow, golden = carbon;apricot = hydrogen).Young S. Kim, Jaheon Kim, Don Kim, and Hee

K. Chae


152 Preparation of Porous Carbon Spheres Dis-persed with Pd–Ag Alloy Nanoparticles

EDX analysis along the cross section revealed

homogeneously in the carbon matrix. that palladium and silver are distributedMasataka Horigome, David A. Pacheco

Tanaka, Margot A. Llosa Tanco, Waki Yukita,Ryo Ishii, Kiyoshi Kobayashi, Fujio Mizukami,and Toshishige M. Suzuki


154 Preparation of Ag Core–Cu Shell Nanoparti-cles by Microwave-assisted Alcohol Reduc-tion Process

12 Microwave Heating

413 K, 5 min1-Heptanol

=

AgO

O

CH2Ag CH3

12O

O

CH2 CH3

12

Microwave Heating

433 K, 5 min1-Heptanol

Ag

O

O

CH2Cu CH3

2 Cu

Takashi Nakamura, Yasunori Tsukahara,Tomohisa Yamauchi, Takao Sakata, HirotaroMori, and Yuji Wada


156 A Facile Size-control Method of CdS Nano-particles In-situ Synthesized in PolymerMatrix by Adjusting Ratio of Acidic Acidwith Metallic Complex in Acrylate Photore-sist Resin

Zheng-Bin Sun, Wei-Qiang Chen, Xian-ZiDong, and Xuan-Ming Duan


158 Photoluminescence Property of TitanateLayered Oxide Intercalated with Tb3þ Ionsby Electrostatic Self-assembly DepositionMethod

Titanate layered oxide intercalated with Tb3+ ions was prepared by electrostatic self-assemblydeposition method using the exfoliated H2Ti4O9 (Ti4O9 nanosheet). The naked Tb3+ greenemission through energy transfer from Ti4O9 nanosheet was observed. The efficiency of theenergy transfer decreased with heat treatment, which results from the decrease in the interlayerdistance.

Tb3+Tb3+

Tb3+

Tb3+ ion (Cation)

Ti4O9-nanosheets(negative charge)

Titanate layered oxideIntercalated with Tb3+

0.80 nm

About 1 µm − 50 nm

Wavelength/nm

Tb3+

emis

sion

(λem

= 5

45 n

m)

Inte

nsity

/ ar

b un

it

450 550 650

As-depo.

350

200 °C

300 °C

Excitationλem = 545 nm

Emissionλex = 315 nm

As-depo.(λex = 315 nm)

250

Shintaro Ida, Chikako Ogata, Taishi Inoue,Kazuyoshi Izawa, Ugur Unal, OzgeAltuntasoglu, and Yasumichi Matsumoto




160 The Crystal Structure of Methylphenylarsin-ic Acid: A Contaminant of Rice Plants andGroundwater

R

R

S A single crystal X-ray study ofmethylphenylarsinic acid, MePhAsO•OH,a contaminant of rice plants and of

lattice the molecules form hydrogen-bondedchains linking O···HO entities; As–O, OH

groundwater, showed that in the crystal

are 1.654(1), 1.719(1) Å.

Eric J. Chan, John S. Edmonds, Kozo Kazawa,Brian W. Skelton, and Allan H. White

162 Catalytic Asymmetric Synthesis and OpticalResolution of Planar Chiral Rotaxane

Yoshimasa Makita, Nobuhiro Kihara, NaohisaNakakoji, Toshikazu Takata, Shinji Inagaki,Chiyo Yamamoto, and Yoshio Okamoto


164 Preparation of Zinc–Homoenolate from�-Sulfonyloxy Ketone and Bis(iodozincio)-methane

Treatment of α-sulfonyloxyl ketone with bis(iodozincio)methane gives a zinccyclopropoxide which is formed via a nucleophilic addition of the reagent tocarbonyl group followed by an intramolecular substitution reaction.

RR'

O

OSO2R"

CH2(ZnI)2R

R'

IZnOCH2 Br

CuCN•2LiCl RR'

O

H2CKenichi Nomura and Seijiro Matsubara


166 The pH Rule for Fabricating CompositeCoCu Nanowire Arrays

0.00.10.20.30.40.50.60.70.20.40.60.8

400

800

1200

1600

(b)

Cu Composition (x)

Hc

(Oe)

Mr/

Ms

pH=3.1pH=3.5

pH=3.3 (a)

40 50 60 700

10002000300040005000600070008000

fcc Cu

hcp Co

(111

)

(87/13)(75/25)(60/40)(49/51)

(Co/Cu = 38/62)

(220

)

(200

)

(220

)

(200

)

fcc CoCu alloy(100

)

Inte

nsi

ty(c

ps)

2θ / degreeAn apparent phase and composition-pH value rule has been found for CoCu nanowireelectrodepositing. A series of composite CoCu nanowires coherently structured in hcp and fccphases (see XRD) can be obtained within a quite large composition range. The specificmagnetic properties, coercivity and squareness of the composite array are increased by threetimes, apparently preceding to those in the single-phase one.

Xiaoxu Liu, Jianling Zhao, Yangxian Li,Shifeng Xu, Zhiyong Zhu, Jinglan Chen, andGuangheng Wu

168 Cu2(C3H2N3O3)2(C10H8N2): A Hydrogen-bonded Assemblies Supermolecule Contain-ing 1D Channels and Novel Two-coordinatedLinear N–Cu–N Configurations

Ji-Min Du and Dae Joon Kang




170 Electronic Structure Analysis of Interfacebetween Support Surface and Cocatalystfor Water Splitting Layer Photocatalyst byDFT Method

The information and the finding about the electronic structure of the interface for thephotocatalyst (NiOx

/K2La2Ti3O10) for water splitting were acquired by the two-dimentionalperiodic boundary condition surface model DFT calculations. The difference in the electronicstates for the interface between the cocatalyst and the photocatalyst was characterized in termsof the crystal surfaces of the support photocatalyst.

K2 La

2 Ti3 O

10

NiNi

K2La2Ti3O10

Ni(111)/K2La2Ti3O10(101) Ni(111)/K2La2Ti3O10(002)

+

H+/H2 (+4.43 eV/vac.)

Vacuum level±0.00 eV

Ni3d level of Ni on K2La2Ti3O10(101)

Co-catalystNi metal

Supported photocatalyst K2La2Ti3O10

Ni3d level of Ni on K2La2Ti3O10(002)

; smooth

At the interface; not smooth

Photoexcitation

H+ reductiondriving force

C.B. (Ti3d) e-

e-

e-

e-

Yoshiki Shimodaira, Akihiko Kudo, andHisayoshi Kobayashi

172 Carbazole Synthesis by Platinum-catalyzedC–H Functionalizing Reaction Using Wateras Reoxidizing Reagent

Treatment of 1-aminobiphenyl and diphenylamine with catalytic amount of Pt/C inhydrothermal water (250 °C, 4 MPa) affords 9H-carbazole in good yield. In this catalytic cycle,water works as reoxidizing reagent for platinum catalyst.

NH2 NHH2O, 250 °C NH

Pt/C (5 mol %) Pt/C (5 mol %)

H2O, 250 °CMitsuru Yamamoto and Seijiro Matsubara


174 Self-assembly of Birnessite Manganese Diox-ide into Monodisperse Honeycomb andHollow Nanospheres Monodisperse honeycomb and hollow

nanospheres of ordered birnessite

manganese dioxide nanoplatelets were

acid and following self-assembly of

produced nanoplatelets.

facilely synthesized in high yields via

the redox reaction of KMnO4 and oleic

Honeycomb MnO2

nanospheresHollow MnO2 nanospheres

O/W emulsion

OilH2O

Oleic acid KMnO4

MnO2 nucleus

Oil Oil

Oil

MnO2 platelet

MnO2 platelet

Hongmin Chen and Junhui He


176 Preparation of Gold and Platinum Nanopar-ticles Using Visible Light Activated FeIII-complex

FeII

O2

O2-

FeIIIRCO2-

CO2

R

Mn+ M(n-1)+ M0

FeIII(RCO2-)n

hv (visible)

+

FeII(RCO2-)n-1(RCO2)

LMCT

R = HO(CH3CO2-)2C or CO2

-

Jaesang Lee, Jungho Ryu, and Wonyong Choi

178 Electron Transfer in Tris(bipyridine)ruthe-nium(II) Complex Films on ITO

Katsuhiko Kanaizuka, Shinji Kato, HiroshiMoriyama, and Chyongjin Pac




180 Chemical Synthesis of Face-centered-tetrag-onal FePt Film Using Sol–Gel Method

A simple sol−gel spin-coating technique was successfully developed to prepare FePt films. Pureface-centered-tetragonal FePt film with moderate hard magnetic performance was obtained bycalcining in oxygen at 370 °C for 5 min and subsequently reducing in hydrogen at 470 °C for35 min.

Hailin Su, Nujiang Tang, Ruilong Wang, BaiNie, Shaolong Tang, Liya Lv, and Youwei Du


182 Application of a Water Soluble Alkoxysilanefor the Formation of Mesoporous Silicafrom Nonionic Surfactant Micelles BearingCholesterol

200 nm

6-7 nm / stripe

20 nm

Shun Takahashi, Yasunari Ikkai, CarlosRodriguez-Abreu, Kenji Aramaki, TetsuOhsuna, and Kazutami Sakamoto


184 N-Terminus Methylation of Desulfovibriovulgaris (Miyazaki) F Cytochrome c3

Shin Iida, Yusuke Kawano, Noriyuki Asakura,Kenji Tabata, Ichiro Okura, and ToshiakiKamachi

186 Fabrication of Nanodispersed Pt–Sn/SBA-16Catalysts and Their Catalytic Applications Nanodipersed Pt−Sn nanoparticle in SBA-16.

MW drying CE drying

Pt–Sn impregnated SBA-16 50nm20nm

Young Kyu Hwang, Deok-Kyu Kim, Ajit SinghMamman, Sang-Eon Park, and Jong-San Chang


188 Oxone-mediated Methoxy Thiocyanation of1,1-Disubstituted Olefins in Methanol

Reactions of 1,1-disubstituted olefins with oxone and ammonium thiocyanate in methanol gavethe corresponding 1-methoxy-2-thiocyano adducts in various yields.

R1=Ph, R2=CH3 2 (in 77% yield) 3 (in 8% yield)

R1

R2

+ NH4SCN (2.2eq)MeOH, rt, 20min R1

R2

SCN

OMe

+R1

R2 SCN

SCN

1

Oxone (1.5 equiv.)

Guaili Wu, Wentao Wu, Rui Li, Yinglin Shen,and Longmin Wu




190 Highly Efficient Plastic Dye-sensitized Photo-electrodes Prepared by Low-temperatureBinder-free Coating of Mesoscopic TitaniaPastes

0

5

10

15

0 0.2 0.4 0.6 0.8

Pho

tocu

rren

t / m

A c

m-2

Voltage / V

η = 6.4% (1/8 sun)

η = 5.8% (1 sun)

Lightweight and flexible plastic TiO2 electrode prepared by the binder-free paste is a powerfulelement for creating low-cost, printable dye-sensitized solar cells.

Yujiro Kijitori, Masashi Ikegami, and TsutomuMiyasaka


192 Solid-state 17ONMR in Biological Solids:Efficient 17O Labeling of Amino Acids andPeptides +

OH

F

F

F

F

F

H217O

SPPS protocol DeprotectionDCC

Anhydrous HOBt

F

F

F

F

F

OC

OC

H R

FmocNH

OHC

O17

C

H R

FmocNHOH17

CO

C

H R

FmocNH

[17O]-amino acids[17O]-peptidesKazuhiko Yamada, Toshio Yamazaki, MiwakoAsanuma, Hiroshi Hirota, Naoki Yamamoto,and Yasuhiro Kajihara

194 Distinctly Different Conformations of anAmorphous Polymer with Azobenzene SideChains in Solid and Solution 1.5

1.0

0.5

0.0

Abs

orba

nce

500400300

Wavelength / nm

1.0

0.5

0.0

Abs

orba

nce

500400300

Wavelength / nm

A cast film and a solution in a good solvent Dispersed solid and a solution in a poor solvent

O O

O

NN

UV

Kunihiro Ichimura and Haruhisa Akiyama

196 Conversion of (sp3)C–F Bonds of AlkylFluorides to (sp3)C–Heteroatom (Hetero-atom = I, SR, SeR, TeR) Bonds by the Useof Magnesium Reagents Having HeteroatomSubstituents

Alkyl–F Z–MgX Alkyl–Z+

(Z = I, TeR, SeR, SR)

Shameem Ara Begum, Jun Terao, and NobuakiKambe


chemistry letters · 8 eﬀective synthesis of 5-substituted buteno-lide derivatives by using...

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